chloral

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/01/16 11:38:15」(JST)

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Chloral

Names
IUPAC name Trichloroethanal
Identifiers
CAS Number	75-87-6 Y
3D model (Jmol)	Interactive image
ChemSpider	6167 Y
ECHA InfoCard	100.000.829
EC Number	200-911-5
KEGG	C14866 Y
PubChem	6407
UNII	FLI06WS32H Y
InChI InChI=1S/C2HCl3O/c3-2(4,5)1-6/h1H Key: HFFLGKNGCAIQMO-UHFFFAOYSA-N
SMILES ClC(Cl)(Cl)C=O
Properties
Chemical formula	C2HCl3O
Molar mass	147.388 g/mol
Appearance	colorless, mobile, oily liquid
Odor	pungent and irritating
Density	1.404 g/cm3
Melting point	−57.5 °C (−71.5 °F; 215.7 K)
Boiling point	97.8 °C (208.0 °F; 370.9 K)
Solubility in water	forms soluble hydrate
Solubility in ethanol	miscible
Solubility in diethyl ether	miscible
Solubility in chloroform	miscible
Acidity (pKa)	9.66
Magnetic susceptibility (χ)	-67.7·10−6 cm3/mol
Refractive index (nD)	1.45572
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)	480 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Chloral, also known as trichloroacetaldehyde or trichloroethanal, is the organic compound with the formula Cl₃CCHO. This aldehyde is a colourless oily liquid that is soluble in a wide range of solvents. It reacts with water to form chloral hydrate, a once widely used sedative and hypnotic substance.

Production

Chloral is produced commercially by the chlorination of acetaldehyde in hydrochloric acid, producing chloral hydrate. Ethanol can also be used as a feedstock. This reaction is catalyzed by antimony trichloride:

H₃CCHO + 3 Cl₂ + H₂O → Cl₃CCH(OH)₂ + 3 HCl

The chloral hydrate is distilled from the reaction mixture. The distillate is then dehydrated with concentrated sulfuric acid, after which the heavier acid layer (containing the water) is drawn off:

Cl₃CCH(OH)₂ → Cl₃CCHO + H₂O

The resulting product is purified by fractional distillation. Small amounts of chloral hydrate occur in some chlorinated water.

Key reactions

Chloral tends to form adducts with water (to give chloral hydrate) and alcohols.

Aside from its tendency to hydrate, chloral is notable as a building block in the synthesis of DDT. For this purpose, chloral is treated with chlorobenzene in the presence of a catalytic amount of sulfuric acid:

Cl₃CCHO + 2 C₆H₅Cl → Cl₃CCH(C₆H₄Cl)₂ + H₂O

This reaction was described by Othmar Zeidler in 1874. The related herbicide methoxychlor is also produced from chloral.

Treating chloral with sodium hydroxide gives chloroform and sodium formate

Cl₃CCHO + NaOH → Cl₃CH + HCOONa

Chloral is easily reduced to trichloroethanol, which is produced in the body from chloral.

Safety

Chloral and chloral hydrate have the same properties biologically since the former hydrates rapidly. Chloral hydrate was routinely administered to patients on the gram scale with no lasting effects. Prolonged exposure to the vapors is unhealthy however, with a LC50 for 4-h exposure of 440 mg/m³.

See also

• Chloral hydrate

References

UpToDate Contents

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• 5. 小児における不眠の問題をもたらす医学的障害 medical disorders resulting in problem sleeplessness in children

English Journal

• Dechlorination of Chloral Hydrate Is Influenced by the Biofilm Adhesin Protein LapA in Pseudomonas putida LF54.

• Zhang W, Huhe, Pan Y, Toyofuku M, Nomura N, Nakajima T, Uchiyama H.SourceGraduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Ibaraki, Japan.
• Applied and environmental microbiology.Appl Environ Microbiol.2013 Jul;79(13):4166-9. doi: 10.1128/AEM.00804-13. Epub 2013 Apr 19.
• LapA is the largest surface adhesion protein of Pseudomonas putida that initiates biofilm formation. Here, by using transposon insertion mutagenesis and a conditional lapA mutant, we demonstrate for the first time that LapA influences chloral hydrate (CH) dechlorination in P. putida LF54.
• PMID 23603683

• Calpain I activity and its relationship with hippocampal neuronal death in pilocarpine-induced status epilepticus rat model.

• Gao H, Geng Z.SourceDepartment of Neurology, Shanghai Jiaotong University Affiliated Sixth People's Hospital, 600 Yishan Road, Shanghai, 200233, People's Republic of China.
• Cell biochemistry and biophysics.Cell Biochem Biophys.2013 Jun;66(2):371-7. doi: 10.1007/s12013-012-9476-5.
• This study aims to establish pilocarpine-induced rat model of status epilepticus (SE), observe the activity of calpain I in the rat hippocampus and the subsequent neuronal death, and explore the relationship between calpain I activity and neuronal death in the hippocampus. Fifty-eight adult male Wis
• PMID 23212179

• Formation of disinfection byproducts upon chlorine dioxide preoxidation followed by chlorination or chloramination of natural organic matter.

• Yang X, Guo W, Lee W.SourceSchool of Environmental Science and Engineering, Sun Yat-sen University, Guangzhou 510275, China. yangx36@mail.sysu.edu.cn
• Chemosphere.Chemosphere.2013 Jun;91(11):1477-85. doi: 10.1016/j.chemosphere.2012.12.014. Epub 2013 Jan 9.
• Chlorine dioxide (ClO2) is often used as an oxidant to remove taste, odor and color during water treatment. Due to the concerns of the chlorite formation, chlorination or chloramination is often applied after ClO2 preoxidation. We investigated the formation of regulated and emerging disinfection byp
• PMID 23312737

Japanese Journal

• 3P-121 LapA, the biofilm adhesin protein, influences dechlorination of chloral hydrate and flagella motility in Pseudomonas putida LF54

• 日本生物工学会大会講演要旨集 65, 218, 2013-08-25
• NAID 110009738068

• The Asymmetric Syntheses of Methyl D-Digitoxoside, L-Oleandrose and L-Cymarose from Methyl Sorbate, an Achiral Precursor

• Chemical and Pharmaceutical Bulletin 60(8), 1076-1082, 2012
• NAID 130001852520

• Assimilative and co-metabolic degradation of chloral hydrate by bacteria and their bioremediation potential(ENVIRONMENTAL BIOTECHNOLOGY)

• Journal of bioscience and bioengineering 111(4), 448-453, 2011-04
• NAID 110008607501

Related Links

• chloralの意味 - goo辞書 英和和英

chloralとは。意味や和訳。[名][U]1 《化学》クロラール.2 《薬学》抱水クロラール(chloral hydrate)：催眠剤. - 40万項目以上収録、例文・コロケーションが豊富な無料英和和英辞典。

• Chloral 75-87-6 | 東京化成工業株式会社

[Chloral] [75-87-6] | 価格や在庫、物性値などの詳細情報ページです。 ... ・川口の在庫は即日，つくばの在庫は2〜3日以内の出荷となります。・詳細につきましては，お手数ですが営業部までお問い合わせください。

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★リンクテーブル★

拡張検索	「alpha-chloralose」「dichloralantipyrine」「acetylglycinamide chloral hydrate」「chloralose」「pentaerythritol chloral」

「alpha-chloralose」

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αクロラロース、α-クロラロース

関

chloralose

「dichloralantipyrine」

　　[★]

ジクロルアンチピリン

関

dichloralphenazone

「acetylglycinamide chloral hydrate」

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アセチルグリシンアミド抱水クロラール

「chloralose」

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クロラロース

関

alpha-chloralose

「pentaerythritol chloral」

　　[★] ペンタエリトリトールクロラール